Hydrochloric Acid → HCID 59629257, compound

HRID 1045302Notes

Reaction equation

HRID 1045302 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9](C4C=CC(C5C=CC6C(=CC=CC=6)C=5)=CC=4)=[CH:10][CH:11]=3)[CH:6]=[CH:5][C:4]=2[CH:3]=1.[CH3:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].[CH2:38]([Li])[CH2:39][CH2:40][CH3:41].C([O:46][B:47](OC(C)C)[O:48]C(C)C)(C)C.Cl.[C:57]1(C)[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>C1COCC1>[CH:34]1[C:33]2[C:38](=[CH:39][CH:40]=[CH:41][CH:32]=2)[CH:37]=[CH:36][C:35]=1[C:57]1[CH:62]=[CH:61][C:60]([C:9]2[CH:8]=[C:7]3[C:12]([C:13]4[CH:14]=[CH:15][C:2]([B:47]([OH:48])[OH:46])=[CH:3][C:4]=4[CH:5]=[CH:6]3)=[CH:11][CH:10]=2)=[CH:59][CH:58]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 8058HexaneHCID 21531Triisopropyl borateHCID 59629116HCID 59629116, compoundHCID 178418339Butyllithium

Product 1

HCID 59629257HCID 59629257, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Under an argon gas atmosphere, a mixture of 15.0 g (32.7 mmol) of 2-bromo-7-(4-(naphthalene-2-yl)phenyl)phenanthrene and 150 mL of dehydrated THF was cooled down to minus 60 degree C. Then, 25.3 ml (39.2 mmol) of hexane solution of 1.55M n-butyllithium was dropped into the mixture while the mixture was being stirred. The reaction mixture was further stirred at minus 60 degrees for 2 hours. The reaction solution was again cooled down to minus 70 degrees C., and 18.4 g (98.0 mmol) of triisopropylborate was dropped into the solution. The reaction mixture was warmed back to room temperature, stirred for 2 hours and left unattended for one night. Subsequently, the reaction mixture was added with aqueous solution of hydrochloric acid while being cooled on an ice bath, and stirred for 1 hour at room temperature. The reaction mixture was added with toluene, and aqueous phase thereof was eliminated. After organic phase thereof was dried with magnesium sulfate, the solvent was distilled away under reduced pressure. By recrystallizing the obtained solid with toluene-hexane, 9.5 g of 7-(4-(naphthalene-2-yl)phenyl)phenanthrene-2-ylboronic acid was obtained at an yield of 69%.

Workup

  1. temperaturewas cooled down to minus 60 degree C
  2. stirringThe reaction mixture was further stirred at minus 60 degrees for 2 hours
  3. temperatureThe reaction mixture was warmed back to room temperature
  4. stirringstirred for 2 hours
  5. waitleft
  6. waitunattended for one night
  7. temperaturewhile being cooled on an ice bath
  8. stirringstirred for 1 hour at room temperature
  9. dry with materialAfter organic phase thereof was dried with magnesium sulfate
  10. distillationthe solvent was distilled away under reduced pressure
  11. customBy recrystallizing the obtained solid with toluene-hexane

Sources & evidence

ORD record
ord-c33020058a2e468d84a3b264358029d5
Source dataset
uspto-grants-2013_10
Patent number
US08568903B2

Reaction notes

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